Methanol → D-Serine methyl ester hydrochloride

HRID 2355457Notes

Reaction equation

HRID 2355457 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].S(Cl)([Cl:10])=O.[CH3:12]O>>[ClH:10].[CH3:12][O:6][C:5](=[O:7])[C@H:2]([NH2:1])[CH2:3][OH:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 5951L-SerineHCID 24386Thionyl Chloride

Product 1

HCID 11446470D-Serine methyl ester hydrochlorideYield 100%

Procedure

To a solution of serine (105 g, 1 mol) in methanol (1200 mL) was added thionyl chloride (87.6 mL, 142.8 g, 1.2 mol) dropwise at 0° C. After addition, the reaction mixture was heated under reflux for 12 h. Volatiles were evaporated to give (R)-2-amino-3-hydroxy-propionic acid methyl ester hydrochloride (155 g, 100%) as a solid that was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 3.71 (s, 3H), 3.79 (m, 2H), 4.08 (s, 1H), 8.51 (br s, 2H).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 12 h
  4. customVolatiles were evaporated

Sources & evidence

ORD record
ord-c8e2f2666cbe4fc6bb2c3adacb2942a0
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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